Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Deoxysugar Synthesis. III. Removal of Vicinal Mesyloxy Groups with Naphthalene-Sodium
TERUO HAYASHINORIKO TAKEDAHIROMICHI SAEKIEIJI OHKI
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Keywords: butirosin
JOURNAL FREE ACCESS

1977 Volume 25 Issue 8 Pages 2134-2137

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Abstract
Naphthalene-sodium reaction of 3, 4-dimesylates of N-protected 2, 6-diamino-2, 6-dideoxy-α-D-glycosides (1a, 1b) resulted in a good yield of 3-eno compounds (2a, 2b). Application of this anion-radical reaction to butirosin 3', 4'-dimesylate (3) gave 3', 4'-dideoxy-3'-one butirosin A (4a) which shows a broad inhibitory activity against bacteria which are both sensitive and resistant to butirosin. Kanamycin 3', 4'-dimesylate (5a) also analogously gave a 3'-eno derivative (6).
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© The Pharmaceutical Society of Japan
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